Hydrochloric Acid → 7-[2-(4-Methyl-3-oxooct-1-enyl)-5-oxocyclopentyl]heptanol

HRID 372050ノート

反応式

HRID 372050 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][C:20](=[O:27])[CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21OCC[O:11]2.Cl>>[CH3:26][CH:21]([CH2:22][CH2:23][CH2:24][CH3:25])[C:20](=[O:27])[CH:19]=[CH:18][CH:17]1[CH2:16][CH2:15][C:10](=[O:11])[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 570760486-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

生成物 1

HCID 570939037-[2-(4-Methyl-3-oxooct-1-enyl)-5-oxocyclopentyl]heptanol収率 43%

反応条件

温度
60 °C

実験手順

A mixture of 6-(7-hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (1.0 g.) and hydrochloric acid (25 ml; 1N) was stirred at 60° C. for 2 hours, cooled to ambient temperature and extracted with diethyl ether. The ether extract was washed with 2N aqueous sodium carbonate solution and water respectively then dried over magnesium sulphate. Removal of the solvent under reduced pressure gave a crude product (0.7 g.) which was purified by preparative thin layer chromatography on silica gel, using a mixture of diethyl ether, ethyl acetate and hexane (2:1:1 v/v) as eluant, to give 7-[2-(4-methyl-3-oxooct-1-enyl)-5-oxocyclopentyl]heptanol (0.38 g.), νmax (liquid film) 3450 cm-1, 1730 cm-1, 1690 cm-1, 1660 cm-1, 1380 cm-1, 995 cm-1 ; λmax. (ethanol) 230 nm (ε = 13,600); Elemental analysis: Found: C, 74.9; H, 11.0%; C21H36O3 requires C, 74.95; H, 10.8%; N.M.R. (approximately 10% solution in deuterochloroform): Triplets at 3.57 δ (J = 6 cycles/sec.) and 0.88 δ, doublet of doublets at 6.81 δ (J = 15.5 cycles/sec. and J = 7 cycles/sec.), doublets at 6.20 δ (J = 15.5 cycles/sec.) and 1.11 δ (J = 7 cycles/sec.), broad singlet 2.0 δ.

後処理

  1. temperaturecooled to ambient temperature
  2. extractionextracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with 2N aqueous sodium carbonate solution and water respectively
  5. dry with materialdried over magnesium sulphate
  6. customRemoval of the solvent under reduced pressure
  7. customgave a crude product (0.7 g.) which
  8. customwas purified by preparative thin layer chromatography on silica gel
  9. additiona mixture of diethyl ether, ethyl acetate and hexane (2:1:1 v/v) as eluant

出典と根拠

ORDレコード
ord-35be1f87b90243f7b977b933c873fae1
出典データセット
uspto-grants-1978_05
特許番号
US04088695

反応ノート

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